Hydrochloric Acid → 1-(4-Methoxyphenyl)3-(4-piperidyl)-2-imidazolidinone

HRID 614369Notes

Reaction equation

HRID 614369 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[C:15]2=[O:27])[CH2:10][CH2:9]1)C1C=CC=CC=1.CO.Cl.[H][H]>[Pd].O>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([N:16]2[CH2:17][CH2:18][N:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[C:15]2=[O:27])=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 233473451-(1-Benzyl-4-piperidyl)-3-(4-methoxyphenyl)-imidazolidin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 233473361-(4-Methoxyphenyl)3-(4-piperidyl)-2-imidazolidinone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 44 g of 1-(1-benzyl-4-piperidyl)-3-(4-methoxy-phenyl)-imidazolidin-2-one, 320 ml of methanol, 130 ml of water and 12 g of a conc. aqueous solution of hydrochloric acid, with the addition of 10 g of a palladium on charcoal catalyst, is hydrogenated at 30° to 40° C and under reduced pressure until 1 molar equivalent of hydrogen has been taken up. Thereafter the catalyst is removed by filtration and the filtrate is concentrated under reduced pressure. The residue is treated with toluene and recrystallised from a mixture of isopropyl alcohol and diethyl ether to yield the 1-(4-methoxyphenyl)3-(4-piperidyl)-2-imidazolidinone with a melting point of 140° C.

Workup

  1. customThereafter the catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. additionThe residue is treated with toluene
  4. customrecrystallised from a mixture of isopropyl alcohol and diethyl ether

Sources & evidence

ORD record
ord-1856a189419848dcbbd6b223f1889f15
Source dataset
uspto-grants-1979_03
Patent number
US04144344

Reaction notes

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